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#$Date: 2023-04-05 01:53:47 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282359 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/27/7712728.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7712728
loop_
_publ_author_name
'Fischer, Paul J.'
'Roe, Charley B.'
'Stephenson, Jasmine N.'
'Dunscomb, Rachel J.'
'Carthy, Camille L.'
'Nataro, Chip'
'Young, Jr, Victor G'
_publ_section_title
;
 Exploring opportunities for tuning phenyltris(pyrazol-1-yl)borate
 donation by varying the extent of phenyl substituent fluorination.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt00735a
_journal_year                    2023
_chemical_formula_moiety         'C18 H11 B F3 Mn N6 O3'
_chemical_formula_sum            'C18 H11 B F3 Mn N6 O3'
_chemical_formula_weight         482.08
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-02-23 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                112.867(2)
_cell_angle_beta                 92.257(2)
_cell_angle_gamma                103.333(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0619(6)
_cell_length_b                   10.3783(7)
_cell_length_c                   13.2434(11)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.06
_cell_measurement_theta_min      2.62
_cell_volume                     983.12(13)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'APEX3, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'Shelxle-(Rev.825)(Huebschle, C. B., 2011)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Photon-II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.050
_diffrn_reflns_theta_min         2.210
_diffrn_source                   micro
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_description       Block
_exptl_crystal_F_000             484
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF/pentane'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   0.7463
_exptl_transmission_factor_min   0.7014
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0368P)²+0.4235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5566
_reflns_number_total             6818
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt00735a2.cif
_cod_data_source_block           22108z
_cod_database_code               7712728
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.61984(15) 0.38762(12) 0.21456(9) 0.0213(2) Uani 1 1 d . . . . .
N2 N 0.66601(15) 0.53514(12) 0.26240(9) 0.0204(2) Uani 1 1 d . . . . .
C1 C 0.76517(19) 0.34558(17) 0.20083(12) 0.0255(3) Uani 1 1 d . . . . .
H1A H 0.770510 0.247553 0.169657 0.031 Uiso 1 1 calc R U . . .
C2 C 0.90802(19) 0.46646(17) 0.23888(12) 0.0279(3) Uani 1 1 d . . . . .
H2A H 1.026087 0.467336 0.238529 0.033 Uiso 1 1 calc R U . . .
C3 C 0.83998(18) 0.58429(16) 0.27710(12) 0.0253(3) Uani 1 1 d . . . . .
H3A H 0.904274 0.683288 0.308458 0.030 Uiso 1 1 calc R U . . .
N3 N 0.34178(16) 0.43582(13) 0.11861(9) 0.0232(2) Uani 1 1 d . . . . .
N4 N 0.40499(15) 0.57950(12) 0.18615(9) 0.0223(2) Uani 1 1 d . . . . .
C4 C 0.2407(2) 0.42874(18) 0.03290(12) 0.0296(3) Uani 1 1 d . . . . .
H4A H 0.181037 0.341383 -0.027890 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2351(2) 0.56692(19) 0.04513(14) 0.0334(3) Uani 1 1 d . . . . .
H5A H 0.172826 0.591918 -0.003719 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3395(2) 0.65962(17) 0.14358(13) 0.0285(3) Uani 1 1 d . . . . .
H6A H 0.361672 0.762310 0.176043 0.034 Uiso 1 1 calc R U . . .
N5 N 0.33474(15) 0.41337(12) 0.32118(9) 0.0206(2) Uani 1 1 d . . . . .
N6 N 0.41161(15) 0.55926(12) 0.36611(9) 0.0201(2) Uani 1 1 d . . . . .
C7 C 0.23361(19) 0.38722(16) 0.39262(11) 0.0239(3) Uani 1 1 d . . . . .
H7A H 0.165287 0.294089 0.382347 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2424(2) 0.51536(17) 0.48406(12) 0.0274(3) Uani 1 1 d . . . . .
H8A H 0.183695 0.527113 0.546544 0.033 Uiso 1 1 calc R U . . .
C9 C 0.35492(19) 0.62105(16) 0.46372(11) 0.0251(3) Uani 1 1 d . . . . .
H9A H 0.387715 0.721648 0.510805 0.030 Uiso 1 1 calc R U . . .
B1 B 0.5276(2) 0.62135(16) 0.29503(12) 0.0203(3) Uani 1 1 d . . . . .
C10 C 0.62689(18) 0.79118(14) 0.35438(11) 0.0217(2) Uani 1 1 d . . . . .
C11 C 0.68277(19) 0.86277(16) 0.46832(12) 0.0262(3) Uani 1 1 d . . . . .
H11A H 0.650544 0.813535 0.514757 0.031 Uiso 1 1 calc R U . . .
C12 C 0.7845(2) 1.00455(17) 0.51436(12) 0.0296(3) Uani 1 1 d . . . . .
F1 F 0.83917(16) 1.07215(13) 0.62429(8) 0.0523(3) Uani 1 1 d . . . . .
C13 C 0.8369(2) 1.07856(16) 0.45009(14) 0.0309(3) Uani 1 1 d . . . . .
F2 F 0.93903(14) 1.21458(10) 0.49476(10) 0.0427(3) Uani 1 1 d . . . . .
C14 C 0.7865(2) 1.00799(19) 0.33754(15) 0.0377(4) Uani 1 1 d . . . . .
F3 F 0.8427(2) 1.08003(16) 0.27507(12) 0.0733(5) Uani 1 1 d . . . . .
C15 C 0.6843(2) 0.86728(18) 0.28963(13) 0.0330(3) Uani 1 1 d . . . . .
H15 H 0.652219 0.821199 0.211546 0.040 Uiso 1 1 calc R U . . .
Mn1 Mn 0.36875(3) 0.27576(2) 0.16817(2) 0.02121(6) Uani 1 1 d . . . . .
C16 C 0.1409(2) 0.18587(16) 0.12706(12) 0.0295(3) Uani 1 1 d . . . . .
O1 O -0.00224(16) 0.12790(14) 0.09771(11) 0.0459(3) Uani 1 1 d . . . . .
C17 C 0.3975(2) 0.14603(16) 0.22237(12) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.4155(2) 0.06573(14) 0.25903(11) 0.0429(3) Uani 1 1 d . . . . .
C18 C 0.4068(2) 0.16215(16) 0.03283(12) 0.0258(3) Uani 1 1 d . . . . .
O3 O 0.42768(18) 0.08875(13) -0.05349(9) 0.0378(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 107.09(12) . . ?
C1 N1 Mn1 132.22(10) . . ?
N2 N1 Mn1 120.50(9) . . ?
C3 N2 N1 109.28(11) . . ?
C3 N2 B1 129.76(12) . . ?
N1 N2 B1 120.94(11) . . ?
N1 C1 C2 110.25(13) . . ?
N1 C1 H1A 124.9 . . ?
C2 C1 H1A 124.9 . . ?
C3 C2 C1 104.83(13) . . ?
C3 C2 H2A 127.6 . . ?
C1 C2 H2A 127.6 . . ?
N2 C3 C2 108.54(13) . . ?
N2 C3 H3A 125.7 . . ?
C2 C3 H3A 125.7 . . ?
C4 N3 N4 106.43(12) . . ?
C4 N3 Mn1 130.54(10) . . ?
N4 N3 Mn1 121.86(9) . . ?
C6 N4 N3 109.56(11) . . ?
C6 N4 B1 132.45(12) . . ?
N3 N4 B1 117.95(11) . . ?
N3 C4 C5 110.65(14) . . ?
N3 C4 H4A 124.7 . . ?
C5 C4 H4A 124.7 . . ?
C6 C5 C4 104.94(13) . . ?
C6 C5 H5A 127.5 . . ?
C4 C5 H5A 127.5 . . ?
N4 C6 C5 108.39(13) . . ?
N4 C6 H6A 125.8 . . ?
C5 C6 H6A 125.8 . . ?
C7 N5 N6 106.76(11) . . ?
C7 N5 Mn1 130.16(10) . . ?
N6 N5 Mn1 122.98(8) . . ?
C9 N6 N5 108.78(11) . . ?
C9 N6 B1 133.55(12) . . ?
N5 N6 B1 117.40(10) . . ?
N5 C7 C8 110.63(13) . . ?
N5 C7 H7A 124.7 . . ?
C8 C7 H7A 124.7 . . ?
C9 C8 C7 104.56(12) . . ?
C9 C8 H8A 127.7 . . ?
C7 C8 H8A 127.7 . . ?
N6 C9 C8 109.26(12) . . ?
N6 C9 H9A 125.4 . . ?
C8 C9 H9A 125.4 . . ?
N2 B1 N6 107.67(11) . . ?
N2 B1 N4 106.95(10) . . ?
N6 B1 N4 104.51(11) . . ?
N2 B1 C10 107.73(11) . . ?
N6 B1 C10 115.82(11) . . ?
N4 B1 C10 113.70(11) . . ?
C11 C10 C15 116.97(13) . . ?
C11 C10 B1 122.68(12) . . ?
C15 C10 B1 119.61(12) . . ?
C12 C11 C10 120.82(14) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
F1 C12 C13 118.15(14) . . ?
F1 C12 C11 120.34(14) . . ?
C13 C12 C11 121.48(14) . . ?
F2 C13 C12 121.24(15) . . ?
F2 C13 C14 120.48(15) . . ?
C12 C13 C14 118.24(14) . . ?
F3 C14 C13 117.74(15) . . ?
F3 C14 C15 120.77(16) . . ?
C13 C14 C15 121.48(15) . . ?
C14 C15 C10 120.96(14) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 Mn1 C18 91.25(6) . . ?
C17 Mn1 C16 90.85(7) . . ?
C18 Mn1 C16 89.00(7) . . ?
C17 Mn1 N1 92.38(6) . . ?
C18 Mn1 N1 92.44(6) . . ?
C16 Mn1 N1 176.43(6) . . ?
C17 Mn1 N5 90.65(6) . . ?
C18 Mn1 N5 177.05(6) . . ?
C16 Mn1 N5 93.23(6) . . ?
N1 Mn1 N5 85.23(5) . . ?
C17 Mn1 N3 175.59(6) . . ?
C18 Mn1 N3 92.72(6) . . ?
C16 Mn1 N3 91.15(6) . . ?
N1 Mn1 N3 85.52(5) . . ?
N5 Mn1 N3 85.31(5) . . ?
O1 C16 Mn1 177.86(14) . . ?
O2 C17 Mn1 178.52(13) . . ?
O3 C18 Mn1 178.72(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3367(18) . ?
N1 N2 1.3596(16) . ?
N1 Mn1 2.0216(12) . ?
N2 C3 1.3551(18) . ?
N2 B1 1.5589(19) . ?
C1 C2 1.397(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.379(2) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
N3 C4 1.3389(18) . ?
N3 N4 1.3639(16) . ?
N3 Mn1 2.0592(12) . ?
N4 C6 1.3536(18) . ?
N4 B1 1.5645(19) . ?
C4 C5 1.391(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.378(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
N5 C7 1.3386(17) . ?
N5 N6 1.3669(15) . ?
N5 Mn1 2.0485(11) . ?
N6 C9 1.3522(17) . ?
N6 B1 1.5617(19) . ?
C7 C8 1.392(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.374(2) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
B1 C10 1.609(2) . ?
C10 C11 1.3974(19) . ?
C10 C15 1.401(2) . ?
C11 C12 1.384(2) . ?
C11 H11A 0.9500 . ?
C12 F1 1.3487(17) . ?
C12 C13 1.371(2) . ?
C13 F2 1.3407(17) . ?
C13 C14 1.375(2) . ?
C14 F3 1.3427(19) . ?
C14 C15 1.378(2) . ?
C15 H15 0.9500 . ?
Mn1 C17 1.8064(16) . ?
Mn1 C18 1.8067(15) . ?
Mn1 C16 1.8100(16) . ?
C16 O1 1.1437(19) . ?
C17 O2 1.1472(19) . ?
C18 O3 1.1459(18) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 0.67(15) . . . . ?
Mn1 N1 N2 C3 -174.86(9) . . . . ?
C1 N1 N2 B1 -177.41(11) . . . . ?
Mn1 N1 N2 B1 7.06(15) . . . . ?
N2 N1 C1 C2 -0.62(15) . . . . ?
Mn1 N1 C1 C2 174.18(10) . . . . ?
N1 C1 C2 C3 0.33(16) . . . . ?
N1 N2 C3 C2 -0.47(15) . . . . ?
B1 N2 C3 C2 177.39(13) . . . . ?
C1 C2 C3 N2 0.09(16) . . . . ?
C4 N3 N4 C6 1.60(16) . . . . ?
Mn1 N3 N4 C6 -167.23(10) . . . . ?
C4 N3 N4 B1 179.48(12) . . . . ?
Mn1 N3 N4 B1 10.66(16) . . . . ?
N4 N3 C4 C5 -1.09(18) . . . . ?
Mn1 N3 C4 C5 166.40(11) . . . . ?
N3 C4 C5 C6 0.19(19) . . . . ?
N3 N4 C6 C5 -1.51(17) . . . . ?
B1 N4 C6 C5 -178.98(14) . . . . ?
C4 C5 C6 N4 0.80(18) . . . . ?
C7 N5 N6 C9 -0.85(15) . . . . ?
Mn1 N5 N6 C9 175.89(9) . . . . ?
C7 N5 N6 B1 -175.73(11) . . . . ?
Mn1 N5 N6 B1 1.00(15) . . . . ?
N6 N5 C7 C8 0.47(16) . . . . ?
Mn1 N5 C7 C8 -175.95(10) . . . . ?
N5 C7 C8 C9 0.08(17) . . . . ?
N5 N6 C9 C8 0.92(16) . . . . ?
B1 N6 C9 C8 174.65(14) . . . . ?
C7 C8 C9 N6 -0.61(16) . . . . ?
C3 N2 B1 N6 -125.97(14) . . . . ?
N1 N2 B1 N6 51.68(15) . . . . ?
C3 N2 B1 N4 122.19(14) . . . . ?
N1 N2 B1 N4 -60.16(15) . . . . ?
C3 N2 B1 C10 -0.40(18) . . . . ?
N1 N2 B1 C10 177.25(11) . . . . ?
C9 N6 B1 N2 131.69(15) . . . . ?
N5 N6 B1 N2 -54.99(14) . . . . ?
C9 N6 B1 N4 -114.82(15) . . . . ?
N5 N6 B1 N4 58.50(14) . . . . ?
C9 N6 B1 C10 11.1(2) . . . . ?
N5 N6 B1 C10 -175.60(11) . . . . ?
C6 N4 B1 N2 -134.20(15) . . . . ?
N3 N4 B1 N2 48.51(15) . . . . ?
C6 N4 B1 N6 111.81(16) . . . . ?
N3 N4 B1 N6 -65.49(14) . . . . ?
C6 N4 B1 C10 -15.4(2) . . . . ?
N3 N4 B1 C10 167.29(11) . . . . ?
N2 B1 C10 C11 -88.80(16) . . . . ?
N6 B1 C10 C11 31.77(19) . . . . ?
N4 B1 C10 C11 152.86(13) . . . . ?
N2 B1 C10 C15 81.06(16) . . . . ?
N6 B1 C10 C15 -158.36(14) . . . . ?
N4 B1 C10 C15 -37.27(18) . . . . ?
C15 C10 C11 C12 2.5(2) . . . . ?
B1 C10 C11 C12 172.64(14) . . . . ?
C10 C11 C12 F1 -179.33(15) . . . . ?
C10 C11 C12 C13 -1.4(2) . . . . ?
F1 C12 C13 F2 -0.3(2) . . . . ?
C11 C12 C13 F2 -178.27(14) . . . . ?
F1 C12 C13 C14 177.63(16) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
F2 C13 C14 F3 -0.2(3) . . . . ?
C12 C13 C14 F3 -178.08(17) . . . . ?
F2 C13 C14 C15 178.77(16) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
F3 C14 C15 C10 179.30(17) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C11 C10 C15 C14 -2.1(2) . . . . ?
B1 C10 C15 C14 -172.49(16) . . . . ?
